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author:

Wu Youxiong (Wu Youxiong.) [1] | Ren Hongyang (Ren Hongyang.) [2] | Wu Yifang (Wu Yifang.) [3] | Wang Bingxi (Wang Bingxi.) [4] (Scholars:王炳喜)

Indexed by:

Scopus SCIE PKU CSCD

Abstract:

Thermally activated delayed fluorescence (TADF) materials are promising for the next generation of organic light-emitting diodes. To realize reverse intersystem crossing (RISC) effectively for TADF molecules requires basically small energy gap (Delta E-ST) between the lowest singlet (S-1) and triplet (T-1) excited states. In this work, 1,8-naphthalimide was selected as a fixed acceptor (A) because of its large rigid conjugate structure with a high radiative decay rate. Twelve naphthalimide-based intramolecular charge transfer (ICT) compounds were constructed by the conjunction of naphthalimide moiety with each of donors (D) including 9,9-dimethyl-9,10-dihydroacridine, phenoxazine, etc. Their energy gaps were calculated with the Gaussian 09 package at TD-DFT level using the optimal Hartree-Fock exchange method reported by Huang Shuping recently. The results show that D-A structure of naphthalimide-based ICT compounds has smaller Delta E-ST and longer starting fluorescence emission wavelengths (lambda) than those for corresponding D-phenyl-A type. However, strong electron donor like 9-(9H-carbazol-3-yl)-9H-carbazole (DCZ) seems to have no significant effect on Delta E-ST and lambda at high CT amount. To achieve small Delta E-ST of these naphthalimide-based ICT compounds, increasing the twisting angle between D and A, together with enhancing electron donating ability of D is found to be a practical strategy to stabilize the energy of the lowest locally-excited triplet state ((LE)-L-3) and substantially lower the energy of its lowest CT triplet excited state ((CT)-C-3). As a result, 4-(9,9-dimethyl-9,10-dihydroacridine)-N-phenyl-1,8-naphthalimide (4b) and 4-(phenoxazine)-N-phenyl-1,8-naphthalimide (5b) show small Delta E-ST of 0.01 eV and 0.02 eV, respectively. Their lambda and oscillator strengths of vertical absorption from ground state (S-0) to S-1 are 575 nm and 0.0002 for 4b, while 621 nm and 0.0025 for 5b, respectively. In addition, the lambda of compound 5b obtained from its photoluminescence curve is 600 nm, which consists with the computed one with an error of 0.07 eV. Therefore, compounds 4b and 5b can be expected to be potential reddish-orange and red TADF emitters.

Keyword:

energy gaps naphthalimide quantum chemical calculation thermally activated delayed fluorescence

Community:

  • [ 1 ] [Wu Youxiong]Fuzhou Univ, Coll Mat Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 2 ] [Ren Hongyang]Fuzhou Univ, Coll Mat Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 3 ] [Wang Bingxi]Fuzhou Univ, Coll Mat Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 4 ] [Wu Yifang]Heze Univ, Dept Chem & Chem Engn, Heze 274015, Peoples R China

Reprint 's Address:

  • 巫友雄

    [Wu Youxiong]Fuzhou Univ, Coll Mat Sci & Engn, Fuzhou 350116, Peoples R China

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Source :

ACTA CHIMICA SINICA

ISSN: 0567-7351

CN: 31-1320/O6

Year: 2015

Issue: 1

Volume: 73

Page: 53-59

1 . 8 4 3

JCR@2015

1 . 7 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:265

JCR Journal Grade:2

CAS Journal Grade:4

Cited Count:

WoS CC Cited Count: 9

SCOPUS Cited Count: 8

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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